What to Wear for Valentine’s Day Part II: The Girlfriend Date

For our second feature in our Valentine’s Day series, we have the Girlfriend Date. This one goes out to all you gents who’ve locked down that wonderful lady you’ve had your eye on. Maybe its the same girl you used your First Date look on! Or maybe you’ve already been dating her for a  while.  Whatever the case is, there’s no need to hold back this time; dress like you.

1.  “Never Stop Impressing” on Christian


Christian steps up his game this time.  He knows the importance of white pants and pairs them with a light blue shirt, adding color, but not standing out too much.  The cream paisly tie works really well, adding a little bit of character but allows his girlfriend to really shine.  That’s very important to do, guys.

“On a second date I would to show my girlfriend that my outfit is just as interesting as I am, while at the same time not wearing a barrage of different colors. It shows that you’re a fun individual while still adding some sophistication to your demeanor.”



Oxford shirts (along with a button down collar) are a great item to be dressed up or down.


Oxford Shirt from H&M, Pants from H&M, Vintage Paisley Tie

2. “Boardwalk Bae” on Ian 


Ian is a game-changer.  Amidst a world of ties and blazers and buttoned up shirts, he goes with typical beach fashion.  Pulling together typical blues and browns, his color pallet just screams cool and casual.  His light khaki shorts are just the right length, ending a bit above the thigh.  Ian’s denim shirt adds texture to his outfit, but he keeps it unbuttoned as an extra layer.  His  unique touch is the Panama Hat, an awesome hat that has lost its touch in modern times.

“If I was going out with my girlfriend or someone I’ve been dating, I’d assume that we are a bit more comfortable with each other and bit more relaxed. I’d choose to wear something like this because it shows that I’m becoming more comfortable with the person, the style is a bit more relaxed than a first date.  There isn’t any stigmatism or nervousness.”


“This is an outfit I would wear for a date to the beach or a picnic. I think it shows how much more accepting I am of her into my life because I’m dressing more relaxed and comfortable.  It takes a little while for me to be a bit more exposed.”


“A lot of my items were from H&M or second hand or cheaper stores.  You don’t have to pay a lot to get a great outfit going.”

Well said, Ian.


Denim Shirt from H&M, Tank Top from Target, Khaki Shorts from H&M

Panama Hat from H&M, Boat Shoes by Sperry-Top Sider, Thrifted Bracelet, Sunglasses from Dollar Tree

3. “I’ve Already Got Her” on Rajesh


Shockingly, Rajesh has the most dressed down outfit.  He wears his wooly cardigan with a plain purple v-neck and khaki jeans; the shoes are suede cap-toes (his “beaters”).  It’s pretty apparent he’s going super-casual with this look.

“So I’ve been dating you for awhile and you’re my girlfriend. I am not gonna dress to impress cause I’d like to believe that regardless of how I dress you’ll still find me attractive. I chose to wear something that is comfortable, looks good, and is versatile to what we may chose to do during the time we are together.”


“I chose a slightly draped style v-neck, skinny jeans, shoes that I can literally do anything in, and a wool oversized cardigan to keep warm or to give her if she gets chilly.”


“Simple and sweet is the name of the game in this outfit.”


Apparently Rajesh’s sock game never takes a break, no matter the outfit.

Cardigan from TopMan, V-Neck from J. Crew, Khaki Jeans from Hot Topic, Socks from H&M, Suede Shoes from Mark Anthony

4.   The “Street Goth” on Tim


On the subject of being you, Tim wears something that just echoes the current trends in fashion.  I don’t know much about streetwear but I do know that black and white is classy as hell.  Instead of wearing a suit with his girlfriend, he utilizes a white, cut-away collar button up with the air tie (no tie!) and a leather jacket to make sure everyone knows he’s taken and he’s clean as heck.  If people don’t know he’s got a girlfriend, just look at his bracelet.  Tim’s shoes are also definitely awesome; just check out that detail!


“This is my ‘go-to’ outfit on the casual side. When I get closer to my girlfriend and she learns more about my personality and quirks, I feel that I can open up and start expressing and defining my personal style, and not by what is typically good looking for the public.”


“This look is inspired by the “street goth” style, but customized to my personal tastes. The style consists of dark colors and minimalistic designs tailored to a modern, slim fit. ‘Street goth’ style can become a bit outrageous at times, so I simplify it into something that I can wear without looking like a Sith Lord. A clean, leather jacket with black jogger pants contrasted with a white long sleeve button, buttoned in the ‘air tie’ fashion.”


“For me I think what pulls the look together are the shoes. If you are going to wear joggers, make sure your shoes are on point and just as clean as the rest of your outfit. I would wear something like this if I’m taking my girl to a night on the town, going to a concert, or browsing the city in general. It says, ‘I’m not going formal, but I can still look to impress while casual.'”

Cut-away collar shirt from TopMan, Leather jacket from Forever21,  Shoes from NIke, Joggers from Publish Brand

5. “Breakfast Sprezza” on Ethan 


Wearing separates is a great alternative to looking fancy.  Here, I wear the combination from one of the preppy looks and spice it up a bit to be more fun.  As always, the khaki chinos have no break and I wear them with vintage spectators to add to the overall hipster-ness of the outfit.  However, the main pop comes in the floral print tie.  You can’t have Valentine’s Day without flowers!


This is way more dressed up than the previous post; however there are less layers and patterns. It’s plain because after you’ve got the girl, you don’t need to stand out anymore.  This outfit would ensure that it’s the lady who gets to shine.  A lot of the colors (besides the tie) are muted and can be complimentary to any bright color your gal might wear.

IMG_0164This date would be great for a day out in the town, not night due the casual nature of this outfit.  The bright colors would be great for a picnic in the park or even a breakfast date, which is my favourite meal.


Florals on florals.


Always remember to take your jacket off  to give if your gal gets cold!

Cotton Jacket from H&M, Shirt from H&M, Floral Tie from Bull+Moose, Khakis from Banana Republic, Vintage Spectators

As you can see, when dressing for your girlfriend there’s so many options to choose from!  You could be situational, comfortable, or dressed up!  However, what’s important is that you stay true to yourself.  If you’re not a person who likes to dress up, then don’t!  Your girlfriend should see the real you, the person she likes, not some facade.  Just know what fits and what looks great on you personally!

So which one was your favourite?  What would you wear on a date with your girlfriend?  Let us know below!


Ethan W.

Street x Sprezza

Photography by Tim M.  

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